Tetrahydrozoline

  • Tetryzoline
  • Tetrahydrozoline
  • 2 - ( 1,2,3,4- tetrahydronaphthalen -1-yl )-2 -imidazole
  • 2- tetralin -1-yl -4 ,5-dihydro -1H-imidazole
  • 2 - [( 1RS ) ( 1,2,3,4- tetrahydronaphthalene -1-yl ) ] -4,5- dihydro -1H-imidazole
  • 2 - ( 1,2,3,4-tetrahydro -1 -naphthyl) -imidazoline
  • 4,5- dihydro- 2-( 1,2,3,4-tetrahydro -1-naphthyl )-1H -imidazoline
  • 84-22-0
  • 522-48-5 (hydrochloride)

R01AA06, R01AB03, S01GA02, S01GA52

Sympathomimetic

α1 -adrenoceptor agonist

  • 200.28 g · mol -1
  • 236.75 g.mol -1 (hydrochloride)

Hydrochloride:

  • Well in water and ethanol
  • Very difficult in chloroform
  • Practically insoluble in ether

Hydrochloride

Attention

  • 335 mg · kg -1 ( LD50, mouse, oral)
  • 252 mg · kg -1 ( LD50, mouse, s.c )
  • 48.1 mg · kg -1 ( LD50, mouse, i.v.)
  • 785 mg · kg -1 ( LD50, Rat, oral, hydrochloride)
  • 35 mg · kg -1 ( LD50, rat, i.v. hydrochloride)
  • 345 mg · kg -1 ( LD50, Mouse, oral, hydrochloride)
  • 39 mg · kg -1 ( LD50, mouse, i.v. hydrochloride)

Template: Infobox chemical / molecular formula search available

Tetryzoline is a chemical compound that acts schleimhautabschwellend and blood vessel narrowing. It is used as a drug to reduce swelling of the mucous membrane of eye irritation and runny nose ( rhinitis). Tetryzolinhydrochloridlösung is applied topically in the form of eye drops, nasal drops or nasal spray.

Pharmacology

Tetryzoline is a sympathomimetic and acts on α - adrenergic receptors of the sympathetic nervous system. This results in vasoconstriction and decongestant. The effect on β -adrenoceptors is weak. The effect on the conjunctiva occurs after a few minutes and lasts 4-8 hours. Tetryzoline is only slightly absorbed in local, used properly and intact epithelium in the rule. In contrast to phenylephrine was observed even after repeated use no or only a slight dilation of the pupils.

Clinical information

Areas of application (indications )

Tetryzoline is displayed for decongestant use in non-infectious conjunctivitis (eg irritation caused by wind, smoke, chlorinated water or allergic irritation) as well as for colds, hay fever and sinusitis. It is also a temporary improvement of sympathetic ptosis ( Hängelid ) was observed.

Adverse effects (side effects)

As adverse effects can often ( 1-10 % of patients) an increased mucosal blood flow at the application site (blood wealth, reactive hyperemia), mucosal burning and dryness of mucous membranes occur. Systemic effects may be manifested in the form of, eg, palpitations, headache, tremor, weakness, sweating, and increased blood pressure. Lengthy nasal blockages were in the use of nose drops and sprays for a long period often (rhinitis medicamentosa, " drug sniffing " ) were observed.

Particularly when infants even when prescribed dosage is a risk that significant effects on the central nervous system such as restlessness, convulsions, respiratory depression or cardiovascular collapse may occur. These undesirable effects are favored, among other things through the permeable blood - brain barrier at this age.

Abuse

With chronic use as a nasal spray, it may by the hypoxic damage to the tissue to necrotic destruction of the nasal mucosa are (rhinitis sicca).

Chemical and pharmaceutical information

Tetryzoline is chiral and has at the 1- position of the tetralin skeleton an asymmetrically substituted carbon atom. Therefore, it may as (R) - are present or (S) -enantiomer. Is used medicinally, the racemate, usually in the form of water-soluble tetryzoline hydrochloride, rarer than tetryzoline phosphate.

Tetryzoline is not verschreibungspflichig.

Trade names

Azolin (IL ), Berberil N, Burnil (TR ) Caltheon (D), Constrillia (F) Diabenyl T, Exrhinin, Eyesine (USA), Ischemol (I), Murine Tears Plus ( USA), Narbel ( J), Nasin ( IL), Oftan - Starine (FIN) Ophtalmin -N, Rhinopront Top ( D) Stilla (IL ), Tetrilin, Tinarhinin (D), Vasopos N, Typinal (IL ), Tyzine (USA), Vidiseptal EDO Sine, Visine (USA), Visine Yxin (D)

Allergopos N, Collypan (CH), collyrium (USA), Efemolin (D, CH), Spersallerg (CH)

Rights

On January 7, 1956, the company Sahyun Labs had to back up several synthesis routes for imidazoline derivatives described in U.S. Patent 2,731,471, including tetryzoline (column 3, Example 2) and tetryzoline hydrochloride (column 2, Example 1). The use as a sedative in veterinary medicine protected himself on July 8, 1958, the Pfizer Inc. by the U.S. Patent 2,842,478th

CAS registry number PubChem Anatomical Therapeutic Chemical Classification System Dangerous Substances Directive (67/548/EEC) Active ingredient Mydriasis Water chlorination Hypoventilation Syncope (medicine) Blood–brain barrier Digital Object Identifier
766405
de